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FinalFall1999Key

FinalFall1999Key - Print your name flSWER KEY 1 Print your...

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Unformatted text preview: Print your name flSWER KEY 1 Print your TA's name . CHEM 2364 Organic Laboratory Final Examination November 29, 1999 Dr. Tamara Nauman Dfiaaafifiaaaa DC) N©T ©PEN Y©UR TEST UNTEL EVERYCQNE HAS A C©1PYE Paim yam mama aad yaar Taaahimg Aaafiafiaatva mama can avaay pagao Print your name AN KEY ' 2 Print your TA‘s name Acegglsaligylic Acid and Caffeine 1) (10 pts.) Describe using a flow diagram how you would separate a mixture of the following two compounds into the pure compounds. neutral compound basic compound ' NI—ICOCH3 NH2 N02 N02 Add DCM and dilute HCl (01' pts. aqueous HCl) and then separate. Qrgm'c Layer Agmus Lager W and NHCOCH3 H20 and NH3+C1" 3 pts. N02 N92 1) Dry over anh. M3504 Add dllute or aq. 2) Evaporate OR distill 1 Pt- NaOH 01' NaHCO3 off DCM d then separate l A ueo e Wm NHCOCH3 DCMand NH2 1 pt. ' Di N02 scard N02 NH2 1) Dry over anh. MgSO4 2) Evaporate OR distill 1 pt. off DCM Emir" Print your name ANSWER KEY 3 Print your TA‘s name Safety 2) (5 pts.) Fill in the blank with the major hazard associated with each chemical. Use the letters associated with the hazards given below. Each chemical has only one major hazard. Choose from: A = flammable, B = corrosive, C = carcinogen, D = toxin Example: acetone ‘ _L ZnC12 B hydrazine C (CH3CO)2O L 1ch aniline l2 toluene in IE Layer Chrgmgtography 3) (10 pts.) Order the following solvents according to their polarities in the table below: ethyl acetate, carbon tetrachloride, acetone, acetic acid, methanol NQN-fl 2LAR lb] 1 ERMEDLATE POLAR carbon tetrachloride acetone methanol ethyl acetate acetic acid 365:? t-Bugzl Chloride 4) (10 pts. total) Explain why reaction of neopentyl chloride (see structure below) with the SN] or 8N2 alkyl halide test reagents is very unfavorable. H3 H3C CHZCJ CH3 (Give 5 pts. for each mechanism description. Remember they don't have to have the answer stated exactly as the answer key but their answer should have the same meaning). The 8N2 mechanism is slow because backside attack is very unfavorable due to steric hinderance caused by the bulky t—butyl group. The 8N1 mechanism is unfavorable because a primary carbocation would form which is very unstable. Print your name ANSWER KEY 4 Print your TA's name k Qualitative Analysis 5) (10p ts. ) What two qualitative analytical tests could be used to distinguish between the following three compounds? List the name of the two tests in the boxes" in the column to the far left. In the boxes under the compounds place a P for a positive and N for a negative result with these tests. (2pts. for each test and 1 pt. each result) 3? SH? ‘Rfi? CH3CHzCH CH3CI-IZCCH2CH CH3CH2CCH2CCHzCI-I3 --_ , FeCl3 (or enol test) m 6) (10 pts. total) For the equation given below: A) (1 pt.) Balance the equation. B) (4 pts.) Calculate the theoretical yield of the product in grams. C) (3 pts.) Calculate the percent yield of the product. D) (2 pt.) Circle the limiting reagent. USE C = 12.01 g/ mole, H = 1.01 3/ mole, O = 16.00 g/ mole, N = 14.01 g/ mole NHZ OOH NH2 if (5:3 @ \NH2 4. ———-—---->- ‘ COOH fi-r-‘NHz O . 1.00 g 0.170g actual yield = 0.785 g MW = 181.16 g/ mole 17.04 g/ mole 180.12 3/ mole 5.52 x 10—3 mole 9.98 x 10'3 mole A) See equation above. B) theoretical yield: 9.98 x 10"3 mole NH3 x 1 mole product = 4.99 x 10"3 mole product 2 mole NH3 4.99 x 10—3 mole product x 180.12 E product 2 0.899 3 product 1 mole product , C) percentyield = M x 100 a 0.285% x 100 = 87.3% theoretical yield 0.899 g Print your name AN §WER KEY 5 Print your TA‘s name 9mm 7) (5 pts.) Give the organic product for the following reactions: (2.5 pts. each) ;>—< em»— die»- 8) (5 pts.) Place the following compounds in decreasing order of ease of nitration: (most easily nitrated is No. 1) S? We, CCH3 —OCI-I3 r 2 No2 A B c o 1 ' 4 3 2 5 a) D$CBE .ADTCBE c) AC?EB d) BAfCE e) CAFED 2 pts. 5 pts. 2 pts. 1 pt. 0 pts. Print your name AN §WER KEY Print your TA's name Fischer Esterification 9) (10 pts.) Why in the procedure for the Fischer Esterification in the lab manual was Dowex 50X 2~100 ion exchange resin added? Dowex 50X 2-100 ion exchange resin is an acid bound to a polymer support which is used as an acid catalyst. An acid catalyst is necessary to increase the rate of the condensation reaction of the carboxylic acid and alcohol to form the ester product. Adipjc Acid 10) (5 pts.) How did you determine that the oxidation reaction was complete in the preparation of adipic acid from cyclohexanone using potassium permanganate? A stirring rod was dipped into the reaction mixture and then was spotted on a piece of filter paper. If the resulting spot contained a purple ring around a brown spot then the reaction still contained unreacted Kmn04 and was thus incomplete. When only the brown spot of mo; was present on the filter paper, then the reaction was complete. 6 Print your name AN SWEE KEY - 7 Print your TA's name Nylon 11) (10 pts.) A graduate student in Dr. Daly's lab wants to prepare the following polymer: —(C1'12)3_C_—NM(CH2 )3_NH H n All he has available is cyclopentanone, 1,3-propanediamine, potassium hydroxide and potassium permanganate. Show the reactions that the student will need to carry out to prepare the desired product. 1) KMnO4, KOH ? if 2 ts ———————> HO-C—(CI-Izh—G-OH P ' 2) RC] l k—Y—J ' 5002 2pts 1 pt. 213$ ? CFC—(CHm‘G‘Cl + HzN—(CH2)3‘NH2 ‘-—v——’ ‘_W———’ 2 pts. 1 pt. ii 11 ]L ”(Gig)3—C——-l\|J—-(CH2)3—NH H n Print your name ANSWER KEY 8 Print your TA‘s name Nit/[R 12) (10 pts.) Treatment of Compound A, C11H1402, with dilute aqueous acid yields compounds B, C7H602, and C, C4H100. Compound B is a crystalline solid and Compound C is a liquid. Compound C gives a positive Jones test and a negative Lucas test. The NMR of compound A is given below. Determine the structures of Compounds A, B and C. NlVIR of Commund A 6 .5 l 1 x l :E E E E 2 H‘s complex 5 H's multiplet 1 H If they don't have the correct structure \—-'-fir—J If they don't have the correct but know that it is an ester, then give 3 ts structure but know that it is a them 1 point. P ' 1° alcohol, then give them 1 pt If they don't have the correct structure but know that it is a carboxylic acid, then give them 1 point. Print your name SWER KEY 9 Print your TA's name Benzo inaco ' col Rearran ement 13) (10 pts.) Fill in the boxes for the following reactions: Print your name AN WER KEY 10 Print your TA‘s name Friedel-g ;rafts 14) (10 pts.) In the Friedel-Crafts alkylation of PhBr the solvent used is PhNOz. Why couldn‘t you use benzene for the solvent instead of PhNOz? EXPLAIN. n i“ RUE-If “(ME-“‘5'“ ill Benzene would undergo Friedel—Crafts alkylalion while PhN02 will not 7 pts. 10 ts because the -N02 group deactivates the ring. 3 pts. p ' { Or for 7 pts., they could have given the equations: (don't give them the full 10 pts.} ess they explain that the -N02 group deactivatee the ring.) O R~C1, AlCli < :> O—Wog ————; no reaction Para Red 15) (5 pts.) Fill in the boxes with the correct reagents or structure: 2 pts. NaN02 ON 2 —-—~——--—-——- OzN 2+0- HCl ' 0.5 pt. _C_2§:__. ozw—O—Brz }2.5pts. mmmmmmm“WWW1§¥WWWWWVWW“MWWW1“M”WWW“: MKWJ'FWWWYflW-‘FP‘TI‘W‘HV [3" NT‘I‘E‘WT‘ “‘3“ .‘ mmmmmmm—W A 4 Print your name SWER KEY 11 Print your TA's name Aldol ConfiensationlDiels-Alder 16) (10 pts.) Propose a synthesis for the following molecule using starting materials from the list given below and any readily available reagents such as HCl, NaOH, H20, etc.) H CHZCE-Ig, //CH2 W O PIT CH3CH2_C'_'I"I CH3CH2C1 HC if i? l? H—C—CI H3C—CH HkCHZ H3C-C—CH3 "- "'1‘“ ”3'1; ..P‘"-tF-'R“'_’F-"i_.-'W 1‘“- ?‘E‘Y‘W W‘WWHWWWMM”WWWW‘TMWWWWUWWW . .322mmmwmaxim"immwmw"man‘mmmwfl“rmvm-Nwmiwa-mwwwwrurwummMinimum:m-nmn-w.-x‘m'wnw-wm-vn-m Print your name AN WER K Y Print your TA‘s name Lidocajng 17) (5 pts.) The functional groups found in the following molecule are: i? —OCH2CH2*~1TT—-CH2CI-13 NH: a) ammonia, ester, 3° amine b) aromatic amine, ketone, ether, 3’ amine ammonia, ketone, ether, 3° amine a aromatic amine, ester, 3° amine 18) (10 pts.) Provide the structure of the product in the box and then draw an arrow pushing mechanism for this reaction. NH2 R W 12 H3C H3 Cl—C-CHZCI H3C HN’CCHZG 4pm 3 . 11in, ff) if" ‘ H3C 3 CP‘C"CH2CI IF/gzmzcl H—+N £01 ——‘—'——"' H3C H3 2 ts. %r—J "3' 00 P 2pm. $3“ fie .. +| /CCH2C1 if: H— HfiaCCHfl HSCU/cm3 ——-————-—-—--—-—-—-—.> H3C 3 . . . , 2pts. ...
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